Total syntheses of the macrolide antibiotics methymycin and vermiculine are proposed. The aglycone methynolide would be a primary objective and is to be approached via the Wittig coupling of a phosphorane, comprising the C1-C8 part of the methynolide backbone, with an aldehyde which embodies the C9-C11 segment. Each part is to be synthesized with proper chirality, resulting in the totally stereodirected synthesis of an acyclic hydroxy acid which, upon lactonization, affords methynolide. Attachment of desosamine at C-3 of the aglycone affords methymycin. Synthesis of the dilactone vermiculine is based upon construction of a cyclohexene, which undergoes oxidative cleavage to an acyclic precursor of the lactone. Condensation of this precursor in head-to-tail fashion or via a linear sequence completes the macrolide ring of this antibiotic.